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  • Sampling bourbon at Old Forester Distillery on Whiskey Row in downtown Louisville
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    Louisville: Bourbon and Thoroughbreds

  • Dining at Bardstown Bourbon Company Distillery’s Bottle & Bond Kitchen and Bar
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    Bardstown and Loretto: Beautiful Small-Town Distilleries

  • Creek views from the deck of the Break Room at Pepper in Lexington
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    Lexington: The Heart of Bluegrass Region

  • Learning about bourbon-making on a guided tour of Woodford Reserve in Versailles
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    Frankfort and Versailles: Artisanal Distilleries and Horse Farms

Thoroughbred racehorse grazing in a field at WinStar Farm in Versailles
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The Ultimate Road Trip to Discovering Kentucky Bourbon Country

By Idoia Gkikas

  • Route distance:
    377.00
  • Suggested Time:
    5 days

Magnificent thoroughbred horses, verdant rolling hills and high-energy bluegrass music are just a few of Kentucky’s hallmarks, but there’s one thing visitors should not miss: a taste of real Kentucky bourbon.

Kentucky is the birthplace of this oaky, flavorful spirit and produces 95% of the world’s supply. Travel by car for a chance to mingle bourbon tours and tastings with a dash of history, culture and entertainment. Don’t forget to bring home a bottle or two to share.

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Sampling bourbon at Old Forester Distillery on Whiskey Row in downtown Louisville
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Louisville: Bourbon and Thoroughbreds

Touch down at Louisville International Airport (SDF), pick up your rental car and discover Louisville, the birthplace of boxer Muhammad Ali and Louisville Slugger baseball bats. Louisville is also the heart of bourbon country in Kentucky. Once lined with 89 distilleries, downtown’s historic Whiskey Row is experiencing a revitalization.

Start with a tour at Evan Williams Bourbon Experience, Kentucky’s first commercial bourbon distiller founded in 1783. Only one barrel of bourbon is distilled here per day. Even if you don’t tour the artisanal distillery, you can still order a cocktail at the trendy ON3 bar. Old Forester Distillery is where George Garvin Brown made the first bourbon sold in a sealed glass bottle in 1870. Learn about the entire distilling process, including a glimpse at barrel making, on a guided tour.

You can’t visit Louisville without hearing about the Kentucky Derby. Check out horse racing-related exhibits and artifacts at the Kentucky Derby Museum; book a behind-the-scenes tour to see the stables and Churchill Downs racetrack. History buffs will love the collection of war relics, historic toy soldiers and bourbon-making exhibits at the Frazier History Museum. Stay close to the action in a downtown hotel before tomorrow’s trip to Bardstown.

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66 km
0.75 hours by car
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Dining at Bardstown Bourbon Company Distillery’s Bottle & Bond Kitchen and Bar
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Bardstown and Loretto: Beautiful Small-Town Distilleries

Expansive Kentucky pastures accompany your view on the short drive to Bardstown, the second-oldest city in the state and Rand McNally’s pick for “America’s Most Beautiful Small Town” in 2012. It’s where you can visit the site that inspired the state’s song, “My Old Kentucky Home.” You’ll feel especially Southern if you stroll the Federal Hill mansion’s pastoral grounds while sipping a mint julep bourbon cocktail.

Though small in size, Bardstown is big on bourbon. See one of the largest producers of Kentucky spirits at Bardstown Bourbon Company Distillery, then enjoy a cocktail and meal at the Bottle & Bond Kitchen and Bar. Don’t miss a stop at Maker’s Mark Distillery, a National Historic Landmark, to see the production of its 170-year-old recipe and famous red wax-dipped bourbon bottle. Want to sample whiskey inside the world’s largest bourbon barrel? You can do just that at the Bourbon Heritage Center at Heaven Hill Distillery.

A vintage train ride and gourmet meal aboard My Old Kentucky Dinner Train is a perfect way to finish the day before heading to Lexington.

97 km
1 hour by car
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Creek views from the deck of the Break Room at Pepper in Lexington
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Lexington: The Heart of Bluegrass Region

Drive the scenic Bluegrass Parkway an hour east to Lexington. The state’s second-largest city, Lexington is known as the Horse Capital of the World and beloved for the toe-tapping sounds of bluegrass music.

For bourbon aficionados, there’s no better place to start than the Distillery District, the former site of the James E. Pepper Distillery that operated from 1879 to 1958. After sitting abandoned for 50 years, the campus has transformed into the city’s bourbon-centric attraction.

On the property, tour the restored James E. Pepper Distillery, followed by a farm-to-fork meal at Middle Fork Kitchen Bar. Afterward, order a drink at the Break Room at Pepper, a local hangout with creek-side views. Dessert is a tasty ice cream cocktail or a scoop of Bourbon & Honey ice cream at Crank & Boom Ice Cream Lounge. For after-sunset entertainment, The Burl offers top musical acts in a former train depot. Bonus: Duck into the adjacent Burl Arcade for pinball, video games and other retro fun.

Traveling with a beer lover? Lexington Brewing & Distilling Company has you both covered – craft brews at Alltech Brewing and whiskey at Town Branch Distillery. Your final stop is the capital city of Frankfort.

40 km
0.75 hours by car
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Learning about bourbon-making on a guided tour of Woodford Reserve in Versailles
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Frankfort and Versailles: Artisanal Distilleries and Horse Farms

Lined with horse farms, the road to Frankfort is as pretty as a picture and the beauty continues in Frankfort. Kentucky's state capital offers a small-town vibe but plenty of attractions, including the elegant State Capitol building, several history and art museums, and paddling adventures on the Kentucky River.

If you have time to visit only one horse farm during your trip, make it WinStar Farm in the nearby city of Versailles. This facility is home to gorgeous thoroughbred stallions, some of which are Kentucky Derby champions. The tour includes a visit to the stables and a shuttle ride around the picturesque property.

Ready to refuel? The Stave Restaurant & Bourbon Bar is popular for its Southern comfort foods – try the deviled eggs or grilled pimento cheese sandwich – and craft cocktails. Blend craft bourbon with history at Woodford Reserve, a 200-plus-year-old National Historic Landmark in the heart of horse country. End with a tour at the Castle & Key Distillery. This historic property features a limestone castle, massive rickhouse, scenic gardens and carefully crafted spirits. Photo opportunities abound at this one-of-a-kind estate. Reserve your tour early.

Frankfort is in between Louisville and Lexington, convenient to either airport for your trip home.

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